Regioselective Synthesis of Polyheterohalogenated Naphthalenes via the Benzannulation of Haloalkynes

Dan Lehnherr, Joaquin M. Alzola, Emil B. Lobkovsky, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

Independent control of halide substitution at six of the seven naphthalene positions of 2-arylnaphthalenes is achieved through the regioselective benzannulation of chloro-, bromo-, and iodoalkynes. The modularity of this approach is demonstrated through the preparation of 44 polyheterohalogenated naphthalene products, most of which are difficult to access through known naphthalene syntheses. The outstanding regioselectivity of the reaction is both predictable and proven unambiguously by single-crystal X-ray diffraction for many examples. This synthetic method enables the rapid preparation of complex aromatic systems poised for further derivatization using established cross-coupling methods. The power and versatility of this approach makes substituted naphthalenes highly attractive building blocks for new organic materials and diversity-oriented synthesis.

Original languageEnglish (US)
Pages (from-to)18122-18127
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number50
DOIs
StatePublished - Dec 7 2015

Keywords

  • benzannulation
  • cycloaddition
  • halogenation
  • polycyclic aromatic hydrocarbons
  • reaction mechanisms

ASJC Scopus subject areas

  • Chemistry(all)

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